What did you want to be when you grew up?

Some of us wanted to be astronauts. Some of us wanted to be penguin trainers.

And a select few, myself included, wanted to be financial planners. Okay, maybe that was just me…

I couldn’t help it! In second grade, for “bring your parents to school day,” a friend’s mother said, “I help your parents afford to take you to Disney!” Hook, line, and sinker. From that day on, I read everything Warren Buffett recommended – Intelligent Investor, Security Analysis, and when college came around, I majored in finance/accounting.

The Moment My Dream Came True – Or Not

Then came the moment of truth – the moment I realized my dream was actually full of shit. Not financial planning per se because I know phenomenal financial advisers I respect very highly. Instead, it was the deeper institution we call “work.”

I remember it like yesterday – I was sitting in the office of a financial services firm for my first interview with Intelligent Investor in hand. The interviewer handed me a piece of paper and said, “Write down eight people who would buy our mutual funds.”

I chuckled, then sank in my chair as I realized she wasn’t joking. Regrettably – I put the names down of all my friends.

But as I drove home, I couldn’t help but think, “I want to help parents afford a trip to Disney, not sell my poor grandmother a mutual fund no different than the one she already has.” 

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As we all can attest, moments like this hurt. Finding out about Santa Claus is rough. Learning most “role models” are actually horrible humans (athletes, politicians, etc.) is rough, too. But learning your childhood dream is nothing more than being a used car salesman … well, that is devastating.

Yet, I didn’t give up just yet. What if it was just a bad interview?

As luck would have it, it was, and the next year, I was interning at a Big 4. Beady-eyed as I looked up at the 32nd floor of one of Boston’s most impressive buildings, I had a good feeling about this! Everyone told me how proud they were – my family, my girlfriend, my school – it was one of the hardest internships to get into, what most called “the dream.”

It had to be better than those god-awful mutual funds, right?

Totally WRONG. A month into the internship, I had the same gulp. Fortunately, it wasn’t a gulp about screwing over my sweet grandmother. It was a gulp about screwing over myself.

It’s not that I was expecting work to be like this….

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But I certainly wasn’t expecting this…..

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Let me be straight – I know I sound like an entitled millennial. Both types of “work” paid well, had great benefits, and are very prestigious, at least according to my University’s recruiting pamphlets. I also know incredible people who are extremely happy in both jobs.

But for me, entitled or not, something just wasn’t right. Not because I believe in the rah-rah crap most of my generation has been silver-spoon fed like chase your dreams … find your passion … change the world. Nor that they were “hard” work (note that I’m writing this at 8:56 pm on a Friday!).

Rather, these opportunities felt like I was forcing a square peg into a round hole. They weren’t for me. I wasn’t motivated by what they had to offer. And the more I contemplated, the more the old adage “work sucks, then you die” started making sense.

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Yet in voicing my concern, EVERYONE told me I was an idiot (in their own colorful language). How dare you step out of line? How can you waste this opportunity? Do you know how many people would want to be in your shoes?

The more people spoke, the more it felt like Santa Claus. Except this lie was expected to become 80% of my life.

Fortunately… I knew about this thing called freelance.

Is work a giant Santa Claus, with various flavors of motivational crap disguising the “life sucks, then you die” reality of life?


Freelance As My Force For Good

Growing up, I wasn’t too good at listening. I wasn’t full-blown Avril Lavigne, but I didn’t do well at doing things I didn’t want to do.

In regards to staying on this prescribed path, I hid it well. I got good grades, landed great internships, but I would sneak out to do this thing called “freelance.” I didn’t know there was a name for it at the time. Nor that it was different. I just knew it as “how can I help” and found it way more exciting than the ice cream stand or getting coffee.

As a freelancer, I did research, generated business plans and financial models, pretty much anything I could teach myself on Google and YouTube. “Clients” ranged from small businesses to executives wanting extra hands to research/develop the business plan for ventures they wanted to start on the side but had no time.

I loved every second of it! I learned a ton. I worked A LOT (9 pm to 2 am were my peak productivity hours).

But work was special to me. I honestly can’t explain why in the confines of a LinkedIn article.

But the work I did transcended pay, and benefits, and “prestige” (there was literally no prestige…). To put it bluntly, the work was more than work, it was my force for good, introducing me to a facet of life that was truly meaningful.


The In’s and Out’s of My Freelance Experience

How did freelance do this?

The short answer, is that it gave me control over the work itself. If a project didn’t seem exciting, or didn’t align with my values, I didn’t do it.

For example, let’s look at my favorite project – saving 75 jobs by generating the research and business plan for a manufacturing private equity group.

A group of manufacturing business owners had a hunch that baby-boomer-owned manufacturing firms were undervalued but couldn’t quite grasp the business opportunity. They had a feeling that work was coming back from overseas due to the rising costs of production (reshoring). They also felt these businesses were an undervalued investment opportunity. But they couldn’t quite bridge the signal from the noise into a business opportunity and didn’t have the time or in-house resources to do so.

Fortunately for me, they trusted a college student. With the direction of one of their Partners, we met for coffee once a week, he would run through his logic, I would take notes, do the research, and then come back in a week and deliver my findings. As the Partner said:

  • “I worked directly with Matt as he gained an understanding of our strategy and vision and in turn he was able to create the needed materials for the business.”

After three weeks of this process, a substantial business opportunity became clear. Specifically for their niche industry:

  • It will be 2-3% cheaper to produce domestically by 2018. 
  • Production is 2.5x more expensive for firms under 20 employees, yet 92% of their industry is baby-boomer-owned businesses under 20 employees.

Without getting too geeky – the opportunity became clear – pursue! And guess who was the best person to create the now needed business plan?  

But the value for me goes beyond the actual work. The value lies in the below quote:

  • “In no small part to his help, we are presently closing on manufacturers that would have had serious issues continuing as viable entities, subsequently saving close to 75 manufacturing jobs.”

That last part always hits me: “subsequently saving close to 75 manufacturing jobs.

The reason it hits me is because this opportunity struck the same nerve as that experience in second grade. This was meaningful to me. It was more than work. It might not have been financial planning, but holy crap, those 75 workers can now take their kids to Disney!

Freelance exposed me to a project where I could use my business background to save 75 manufacturing jobs. It might not have been pay or prestige, but the meaning from this project eclipsed my two earlier experiences in financial services and the Big 4.

This project wasn’t a one time thing.

Over and over, I found freelance projects that were overwhelmingly fulfilling. Did they pay like the Big 4? Nope. But freelance provided something money can never buy – the opportunity to do meaningful work.

Along with exposing me to various roles and skills and numerous management styles (I had a new boss for every project – some good, some horrible), freelance exposed me to a platform for meaningful work. I didn’t realize it at the time, but the opportunity to do work that really mattered to me was the springboard that accelerated my career.

Today, I sit in a job as a full-time employee that has just as much, if not more, meaning than any of my freelance gigs. I work with amazing people on amazing projects. And I credit the access to this opportunity directly to freelancing being my force for good. 

For More: My Next Big Challenge 

Work doesn’t have to be Santa Claus. For me – freelance was my force for good – introducing me to meaningful work.


My Story is NOT UNIQUE

At the end of this article, you’ll see four examples of how freelance can be YOUR force for good. You’ll see how freelance can empower:

  1. Your path to your dream job
  2. Your path to your dream career
  3. Your path to reinvent your career
  4. Your path to create social good

BUT hold up! Let’s level set.

While we so often use huge buzzwords – “future” of work, “gig” economy, human cloud – for myself and others in my generation, freelance is normal, it’s how we’re used to working. Up until we hit the “working world,” we’re pretty much freelancers without pay. We take multiple classes at a time. Each class has task-based output (homework, book reports, science fairs, etc.). And just like the public ratings/reviews captured on freelance platforms (what I call the our “Being a Product on Amazon”), our ratings/reviews are consolidated into our GPA. 

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Replace classes with clients, homework/projects with deliverables, and GPA with public ratings/reviews, and the freelance economy is just student life with pay.

Which explains why 47% of millennial’s already freelance, and 74% say they’re interested in this lifestyle.

This is just the start. As project-based, or experiential, learning increasingly takes hold across curriculum’s, freelancing doesn’t seem so revolutionary. Instead, we see the potential for the coming generations to say: “We’ve always done it this way.”

My freelance for good experience is NOT unique. For my generation, freelance is normal. It’s what we’re used to. Replace classes with clients, a GPA with public ratings/reviews, and most importantly, a letter grade with a paycheck, and for the coming generations, freelance looks like “the way we’ve always done it.” 


Freelance As YOUR Force For Good

I speak daily with friends and colleagues who have experienced freelance as their force for good. Some are students. Some are full-time employees. Some are full-time freelancers. Some are everything in between.

Here are a few examples.

Example 1: Path to Your Dream Job

In Sarah Kessler’s book Gigged, she introduces us to a developer named Curtis who started freelancing on the software development freelance platform Gigster. Before freelance, Curtis was an above-average developer but far from his dream of working at SpaceX.

Yet as Kessler told us:

  • “Working at SpaceX had been Curtis’s dream: something he thought about in an abstract way but never imagined would be a realistic option. Then, one day in May, he had finished his freelancing work at the coffee shop and realized something had changed. He’d spent the last year teaching himself, through freelance work, how to tackle a broader range of projects. And suddenly he felt qualified.”

Curtis got the job, and as Kessler said:

  • “The time Curtis spent freelancing had provided him with not only the new skills he needed to land his dream job, but a new sense of security.”

Example 2: Path to Your Dream Career

Every time I’m at a university, the inevitable question pops up:

“Is my college degree even worth it?”

My answer is “If you’re a senior, then probably not. If you’re a freshman, you still have time.” 

Let me be clear, I LOVE universities. They brought us unparalleled levels of prosperity, uplifting entire generations from the farm to the factory to the office. 

But in the current state, it’s no secret that they don’t work. How could they? The “close your eyes, throw a dart at the major board, and 4 years, $200k in debt later, you’ll either be underemployed or choose a career you’ll switch from after a year” is a relic of a former assembly line driven time.

What if rather than the above, students did freelance projects – “micro-internships” – in conjunction with the curriculum. Projects could last a couple hours, a couple days, or a couple weeks. With each project, students learn the roles, industries, and potentially the companies they’d want to work for.

As founder Jeffrey Moss of Parker Dewey said:

  • “By providing ways for students to understand the crosswalks from the classroom to a career through project-based work, and for prospective employers to see these skills in action, we can address the challenges facing employers and Career Launchers alike.”

For example, Noel, a Dell Scholar, was the first in his family to attend college. Unfortunately, he didn’t have the network to fully appreciate all the career options available, and his GPA often caused him to be filtered out by prospective employers. Here’s his story in his own words:

“My first micro-internship was a sales outreach project. During this experience, my versatility and organizational skills grew, and I learned to balance life, academics, and real-world projects. My confidence grew as well, so I began to take on jobs that I would have never had the courage to tackle previously.

I have now completed 14 different projects on Parker Dewey and counting. I have written lesson plans for the science curriculum of a charter school in California, completed sales research and lead-generation projects, and verified the translation of a manual in Spanish. I have worked with people all over the world from India to Mexico to Chicago. Each project has given me indispensable knowledge about myself and the real world that I otherwise would have never attained. It has been a lot of hard work where I have put in countless hours, but it has given me a new level of confidence in my abilities as a professional.

I went from not being able to attain a single opportunity, let alone an interview, to having over 10 interviews and a handful of full-time job offers. I used this newly acquired confidence to land a full-time position when I graduate from Texas A&M University this upcoming May 2019 with my Bachelors of Science in Chemical Engineering. This was all in one year. One year! It is insane for me to think how much my life changed with the right opportunity. I never would have imagined all this being possible. For me, the college-to-career transition had been one of the most difficult challenges in my life, but thanks to such a unique idea and well-designed platform, I was able to not only grow as a person but also as a professional.”

I’d be lying if I said I haven’t welled up from a Nicholas Sparks movie.

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But nothing compares to these words from Noel:

“Through these micro-internships, I was able to get in the door and show employers that I had the grit, skills, and ambition.”

The reason is that I can relate to Noel. While I was a student, I felt overwhelming pressure to succeed. I needed to get good grades, get the perfect internship, yet opportunity seemed light years away for us non-Ivy Leaguers. I will never forget applying for consulting internships. Most portal’s asked where you went to school, and if there was a drop down menu my state school was never on it.

But freelance didn’t ask what school I went to. It asked what value I could add. And with each project, my value increased exponentially. To the point that I started taking on challenges I never would have imagined pre-freelance. 

Like Noel, freelance was my force for good in fighting for opportunity.

Freelance provides students with a crosswalk from classroom to career by exposing them to various skills, industries, and companies, all while democratizing access to opportunities once reserved for only “elite” degrees.


Example 3: Path to Reinvent Your Career

Students and software developers are sexy and freelance candy.

But they’re not reality. The reality is that most of us can’t slum it on a friend’s couch if a client doesn’t pay or we can’t find clients. Likewise, we’re not all software developers, an elite class holding the power in a massive talent shortage whether it be freelance or full-time opportunities.

Could freelance really be a force for good for the reality of the world?

Let’s ask Samantha, a former executive of a publicly traded company. She left her cushy and comfortable position to raise a family.

When it was time to reenter the workforce, Samantha recertified in the necessary areas and updated her resume. After spending a few months with no leads, she contacted a recruiting firm. The first person she spoke with told her flat out that she would never get a corporate job because she had been out of the market too long. She spoke with the CEO of another firm and was told basically the same thing, except less bluntly.

Undeterred, she created her own path. One of the books she used to study for her re-certification contained a wealth of knowledge, but unfortunately, it was poorly written by a non-native English speaker. She tracked down the author in India and offered to edit the book for free if he would put her name on the book as the editor. He reluctantly agreed. Halfway through the editing process, he asked her to edit his current book as a paid gig. With her new job in the Gig Economy launched, she found Upwork, reinvented her career, and never considered another corporate 9-5 job.

According to Samantha:

  • “Without the Gig Economy, I don’t think I would have found a job to utilize my technical, coaching, and writing skills. But today, I accept gigs because I want them not because my boss assigned them. If I want to travel, I don’t ask for vacation time. I merely pack my laptop and off I go. I only wish I had found it sooner.”

I found Samantha through Upwork in the spring of 2018. For the next year, she was indispensable both as an editor and as a project manager. 

For More: The Power of Freelance Teams

But more important than any “scoped work,” she became an incredible friend and helped me grow as a writer.

And this past January, when I asked if she had time for an upcoming project, she responded, “I’d love to take a look, but for scoped work, I’m booked until April.”

How incredible is that!?!?! Talk about freelance as a force for good.

Samantha, a tenured executive, used freelance to reinvent her career. Rather than being told she’d never have the same opportunities as before she took time to raise her kids, she started freelancing as an editor. A damn good one at that.


Example 4: Path to Social Good

Currently, work is based around money. You do good work, and I give you a good salary and benefits.

But what if there were more to work than money? I believe it’s an invalidated hypothesis that we all work for money. There’s plenty of research around intrinsic motivation and how work only becomes work once we put money at the center of it. My favorite example is teachers. Some of my favorite humans are teachers, and while they do have entire summers off (that’d be pretty sweet), they aren’t paid what they are worth. If all of us were driven by money alone, we’d be investment bankers NOT teachers.  

So, what if a freelance project could capture the benefits of work while providing a good salary and benefits? Maybe the value of freelance could be capturing your hard work through ratings/reviews, building your network, or the project itself?

That’s the power of Shared Harvest Fund – a platform that connects students and professionals to freelance-based social causes. 

For example, one of my early projects was revising a prior denied grant for employee training. The sad truth was that 15 workers were about to lose their jobs unless we could generate $100k from the Massachusetts Workforce Training Fund. I wasn’t an expert grant writer. Nor a lawyer. I was just a student with decent writing skills who could go to the grant’s website, learn what the grant truly cared about, and reflect their objective and terminology in each one of our answers.

Think of all the nonprofits that could benefit…

According to Nana B.A.M, Founder/CEO of Shared Harvest Fund:

  • “We believe that everyone has a social cause that they’re willing to champion. Shared Harvest is changing how millennial’s pay off their college debt by creating a virtuous cycle of generosity where every good deed done for a nonprofit helps to pay off their student loans. Yep, volunteers who love to give back can make it count. We let you choose to which causes you care about, get connected to organizations that need your talents and then we pick up the tab. It’s that simple. DebtfreelancerTM volunteer marketplace helps you use your super power and #heartwork to slay your dragon and change the world!”

How cool is that!? And as an added bonus, those on the Shared Harvest Platform can use these projects to reduce their student debt! BOOM!



So, what did you want to be when you grow up?

An astronaut? A penguin trainer? A financial advisor?

Whatever it is, I hope freelance can be your force for good to make that happen 🙂  

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CEO of Venture L, Author of The Human Cloud

Matthew R Mottola is a global leader on the Human Cloud - the transition from physical and full time work to digital, remote, independent models.

At Microsoft, in joint partnership with Upwork, he built the Microsoft 365 freelance toolkit - the unlock for enterprises to embrace the human cloud at scale - bringing Microsoft from nascent to an industry leader in under two years.

At Gigster, he built Ideation - enabling freelance developers, data scientists, and product managers to consistently generate what should be built in the software development lifecycle.

His work has been featured by Forbes and Fortune to name a few. He is an international keynote speaker, speaking at leading conferences Remote Work Summit and YPO’s Innovation Week to name a few. He is the author of StartUp Not StartDown, upcoming book The Human Cloud, and contributor to leading industry reports.